1-(benzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)propan-1-one | 1038516-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(benzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)propan-1-one
• 英文别名: 1-(2H-1,3-Benzodioxol-5-YL)-3-(pyridin-2-YL)propan-1-one；1-(1,3-benzodioxol-5-yl)-3-pyridin-2-ylpropan-1-one
• CAS: 1038516-85-6
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: MOFYNGCVZYGMJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  伯吉斯试剂 、 1-(benzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)propan-1-one 以 四氢呋喃 为溶剂， 反应 0.5h， 以67%的产率得到methyl ((3-(benzo[d][1,3]dioxol-5-yl)indolizin-1-yl)sulfonyl)carbamate
  参考文献：
  名称：

  A Synthesis of N-Bridged 5,6-Bicylic Pyridines via A Mild Cyclodehydration Using the Burgess Reagent and Discovery of A Novel Carbamylsulfonylation Reaction

  摘要：

  Cyclodehydration using the Burgess reagent provided a novel approach toward the synthesis of N-bridged 5,6-bicylic pyridines including pyrolo-, imidazo-, and triazolopyridines under mild and neutral conditions. The methodology tolerates acid-sensitive functional groups. A novel addition product was observed between the resulting pyrrolo- or imidazopyridine and an additional equivalent of the Burgess reagent, producing the corresponding sulfonylcarbamate adduct.

  DOI：

  10.1021/ol8011748
• 作为产物：
  描述：

  1-(1,3-Benzodioxol-5-yl)-3-pyridin-2-ylprop-2-en-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 18.0h， 以90%的产率得到1-(benzo[d][1,3]dioxol-5-yl)-3-(pyridin-2-yl)propan-1-one
  参考文献：
  名称：

  A Synthesis of N-Bridged 5,6-Bicylic Pyridines via A Mild Cyclodehydration Using the Burgess Reagent and Discovery of A Novel Carbamylsulfonylation Reaction

  摘要：

  Cyclodehydration using the Burgess reagent provided a novel approach toward the synthesis of N-bridged 5,6-bicylic pyridines including pyrolo-, imidazo-, and triazolopyridines under mild and neutral conditions. The methodology tolerates acid-sensitive functional groups. A novel addition product was observed between the resulting pyrrolo- or imidazopyridine and an additional equivalent of the Burgess reagent, producing the corresponding sulfonylcarbamate adduct.

  DOI：

  10.1021/ol8011748

文献信息

• 一种从芳香酸直接制备芳香酮的方法
  申请人：南京大学

  公开号：CN108912042B

  公开（公告）日：2022-08-19

  一种制备芳基酮的方法，它是以芳香羧酸(ArCOOH)和烯烃为原料，三苯基膦作为脱氧剂，在蓝光灯照射下，在二氯甲烷和水的溶液中，氩气气氛下，在少量磷酸氢二钾存在下，以[Ir(dF(CF3)ppy)2(dtbbpy)]PF6为光催化剂，得到芳香酮化合物。该方法原料易得，反应条件温和，适应性广泛。
• Isolation and Characterization of Regioisomers of Pyrazole-Based Palladacycles and Their Use in α-Alkylation of Ketones Using Alcohols
  作者：Ramesh Mamidala、Shaikh Samser、Nishant Sharma、Upakarasamy Lourderaj、Krishnan Venkatasubbaiah

  DOI：10.1021/acs.organomet.7b00478

  日期：2017.9.11

  palladacycles (1 and 2) were synthesized by the aromatic C–H bond activation of N/3-aryl ring. The application of these regioisomers as catalysts to enable the formation of α-alkylated ketones or quinolines with alcohols using a hydrogen borrowing process is evaluated. Experimental results reveal that palladacycle 2 is superior over palladacycle 1 to catalyze the reaction under similar reaction conditions

  3,5-二苯基-1-（4-（三氟甲基）苯基）-1 H-吡唑基四氢呋喃环化合物（1和2）的区域异构体是通过N / 3-芳基环的芳族C–H键活化合成的。评估了这些区域异构体作为催化剂的应用，以使用氢借入过程与醇形成α-烷基化的酮或喹啉。实验结果表明，在相似的反应条件下，Palladacycle 2在催化反应方面优于Palladacycle 1。Palladacycles 1和2的反应机理使用密度泛函理论（DFT）方法研究了苯乙酮催化的α-烷基化反应。DFT研究表明，对于烷基化反应，Palladacycle 2具有比Palladacycle 1更低的能垒，这与在实验中看到的Palladacycle 2更好的催化活性是一致的。发现palladacycle-phosphine系统具有宽泛的官能团，可作为无溶剂条件下合成α-烷基化产物的有效方法。此外，合成方案已成功应用于从简单的起始原料制备多奈哌齐（一种用于治疗阿尔茨海默氏病的药物）。
• A Synthesis of <i>N</i>-Bridged 5,6-Bicylic Pyridines via A Mild Cyclodehydration Using the Burgess Reagent and Discovery of A Novel Carbamylsulfonylation Reaction
  作者：Jie Jack Li、James J. Li、Jun Li、Ashok K. Trehan、Henry S. Wong、Subramanian Krishnananthan、Lawrence J. Kennedy、Qi Gao、Alicia Ng、Jeffrey A. Robl、Balu Balasubramanian、Bang-Chi Chen

  DOI：10.1021/ol8011748

  日期：2008.7.3

  Cyclodehydration using the Burgess reagent provided a novel approach toward the synthesis of N-bridged 5,6-bicylic pyridines including pyrolo-, imidazo-, and triazolopyridines under mild and neutral conditions. The methodology tolerates acid-sensitive functional groups. A novel addition product was observed between the resulting pyrrolo- or imidazopyridine and an additional equivalent of the Burgess reagent, producing the corresponding sulfonylcarbamate adduct.